Triethylamine → HCID 58530056, compound

HRID 451290Notes

Reaction equation

HRID 451290 reaction equation
[O:1]=[C:2](Cl)[O:3][C:4]([Cl:7])([Cl:6])[Cl:5].[CH2:9]([O:16][NH:17][C@H:18]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C@H:20]([C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>ClCCl>[CH2:9]([O:16][N:17]([C:2]([O:3][C:4]([Cl:7])([Cl:6])[Cl:5])=[O:1])[C@H:18]1[CH2:22][N:21]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[C@H:20]([C:30]([O:32][CH2:33][CH:34]=[CH2:35])=[O:31])[CH2:19]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 58530036HCID 58530036, compound

Product 1

HCID 58530056HCID 58530056, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Diphosgene (0.1 mL, 0.804 mmol) was added slowly to a solution of 2-allyl 1-tert-butyl (2S,4R)-4-[(benzyloxy)amino]pyrrolidine-1,2-dicarboxylate (261 mg, 0.745 mmol) and triethylamine (0.13 mL, 0.933 mmol) in dichloromethane (4 mL) at 0° C. The reaction mixture was stirred at 0° C. for 4 hours then allowed to stand at room temperature overnight. The reaction mixture was chromatographed on silica gel eluted first with hexane then with 4:1 hexane:ethyl acetate to afford the title compound as a clear gum.

Workup

  1. waitto stand at room temperature overnight
  2. customThe reaction mixture was chromatographed on silica gel
  3. washeluted first with hexane

Sources & evidence

ORD record
ord-79dba92cb73542feb3750190f15a59e6
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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